US5847035A - Substituteed tetrahydropyrimidine derivatives and their use as polymerization inhibitors for vinyl aromatic compounds - Google Patents
Substituteed tetrahydropyrimidine derivatives and their use as polymerization inhibitors for vinyl aromatic compounds Download PDFInfo
- Publication number
- US5847035A US5847035A US08/816,630 US81663097A US5847035A US 5847035 A US5847035 A US 5847035A US 81663097 A US81663097 A US 81663097A US 5847035 A US5847035 A US 5847035A
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- Prior art keywords
- hydrogen
- substituted
- tetrahydropyrimidine
- alkyl
- oxyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3462—Six-membered rings
Definitions
- This invention relates to substituted tetrahydropyrimidines and, in particular, the nitroxyl and hydroxy derivatives thereof, and the use of these derivatives as polymerization inhibitors for vinyl-containing and vinyl aromatic compounds and as polymer stabilizers.
- Vinyl aromatic compounds such as styrene, the vinyl benzenes, the substituted styrenes and other vinyl group containing monomers and compounds have a pronounced tendency to undergo spontaneous polymerization during storage, shipping or processing as a result of an elevation in temperature and/or the random generation of free radicals. Since vinyl aromatic compounds produced by the usual industrial methods contain by-products and impurities, these compounds must be subjected to separation and purification processes in order to be suitable for further industrial applications. Such separation and purification is generally accomplished by distillation techniques. In order to inhibit or prevent polymerization of vinyl aromatic monomers during the distillation purification process or, for that matter, their premature polymerization at any time, various polymerization inhibitors for such monomers have been developed and/or proposed for use.
- vinyl aromatic polymerization inhibitors are those described in, among others, U.S. Pat. Nos. 4,040,912; 4,252,615; 4,409,408; 4,457,806; 4,465,882; 4,654,451; 5,312,952; and, 5,540,861.
- U.S. Pat. No. 5,254,760 discloses nitroxyl compounds useful as polymerization inhibitors for vinyl aromatic compounds such as styrene.
- the nitroxyl compounds conform to the general formula ##STR2## wherein each R is alkyl and T is a group required to complete a 5- or 6-membered ring.
- nitroxyl compounds include 1-oxyl-2,2,6,6-tetramethylpiperidine, 1-oxyl-2,2,6,6-tetramethylpiperidin-4-ol, 1-oxyl-2,2,6,6-tetramethylpiperidin-4-one, 1-oxyl-2,2,6,6-tetra-methylpiperidin-4-yl acetate, 1-oxyl-2,2,6,6-tetra-methylpiperidin-4-yl 2-ethylhexanoate, 1-oxyl-2,2,6,6-tetra-methylpiperidin-4-yl stearate, 1-oxyl-2,2,6,6-tetra-methylpiperidin-4-yl benzoate and 1-oxyl-2,2,6,6-tetra-methy;piperidin-4-yl 4-tert-butyl-benzoate.
- U.S. Pat. No. 4,665,185 discloses hydroxyl compounds useful as polymer stabilizers for polyolefins, polyesters, polyurethanes, and for conjugated diene polymers.
- the hydroxyl compounds conform to the general formula ##STR3## wherein E 1 , E 2 , E 3 , and E 4 are independently an organic radical and T is a divalent group required to form a cyclic 5- or 6-membered ring.
- Specific hydroxyl compounds include di(1-hydroxy-2,2,6,6-tetramethylpiperoxidine-4-yl)sebacate and N-(1-hydroxy-2,2,6,6-tetramethylpiperidine-4-yl)- ⁇ -caprolactam.
- substituted tetrahydropyrimidine derivatives having the general formula ##STR4## wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 , which may be the same or different, are hydrogen or alkyl, aryl, cycloalkyl, alkaryl, aralkyl or heterocyclic, or substituted derivative thereof, R 6 or R 7 can additionally be --OH or NR 8 where R 8 is hydrogen, alkyl, aryl, cycloalkyl, alkaryl, aralkyl or heterocyclic, or substituted derivative thereof, or R 6 and R 7 together can be ⁇ O or ⁇ NOH, and any two R groups on the same or adjacent carbon atoms can be joined in a cyclic configuration, and X is oxyl or hydroxy, it being provided that at least one of R 2 and R 3 and at least one of R 4 and R 5 is other than hydrogen, preferably R 2 , R 3 , R
- substituted tetrahydropyrimidine compounds of this invention and their mixtures are useful as polymerization inhibitors for vinyl aromatic compounds such as styrene
- those derivatives in which X is oxyl, i.e., the nitroxyl radical derivatives, are preferred for this use.
- the compounds in which X is hydroxy are also useful as stabilizers for polymers, e.g., polyolefins, polyethers, polyurethanes, etc.
- the substituted tetrahydropyrimidine derivatives of this invention can be obtained by the oxidation of known substituted tetrahydropyrimidine compounds to provide the corresponding nitroxyls.
- the hydroxy derivatives can be obtained from the nitroxyls via reduction or directly from the 1,2,5,6-tetrahydropyrimidine compounds by oxidation.
- the starting substituted tetrahydropyrimidines and their preparation are disclosed in U.S. Pat. No. 4,085,104, the contents of which are incorporated by reference herein.
- These substituted tetrahydropyrimidine derivatives possess the general formula ##STR5## wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are the same as defined above.
- Useful alkyls include methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, escosyl, docosyl, and the like, containing, e.g., up to about 25 carbon atoms, preferably no more than about 18 carbon atoms and more preferably no more than about 12 carbon atoms.
- Useful cyclohexyls include cyclopentyl, cyclohexyl, etc. and derivatives thereof such as alkylcyclohexyl, dialkylcyclohexyl, and the like.
- Aryl, alkaryl and aralkyl include phenyl, alkylphenyl, polyalkylphenyl, chlorophenyl, alkoxyphenyl, naphthyl, alkylnaphthyl, benzyl, substituted benzyl, and the like.
- a preferred starting substituted tetrahydropyrimidine compound for making the nitroxyl and/or hydroxyl derivatives of this invention is 2,2,4,6,6-pentamethyl-1,2,5,6-tetrahydro-pyrimidine (acetonin).
- the foregoing substituted tetrahydropyrimidines can be converted to the corresponding nitroxyl derivatives by catalytic oxidation employing, e.g., a hydroperoxide oxidizing agent as disclosed in U.S. Pat. No. 4,665,185, the contents of which are incorporated by reference herein.
- the nitroxyl derivatives can be reduced to provide the corresponding hydroxy derivatives.
- the reduction of the nitroxyl derivatives to the hydroxy derivatives can be accomplished by catalytic hydrogenation employing a noble metal or nickel catalyst or by a reduction using zinc, borane, hydrazine hydrate or other conventional reducing agent.
- the hydroxy derivatives can be converted to the corresponding nitroxyl derivatives employing a suitable oxidation procedure, e.g., the oxidation of the hydroxyl derivative with manganese oxide in ethyl acetate or ether.
- the substituted tetrahydropyrimidine derivatives of this invention, and advantageously the nitroxyl derivatives, when employed as polymerization inhibitors for vinyl aromatic monomers can be introduced into the vinyl aromatic monomer to be protected by any conventional method.
- the inhibitor is generally introduced just upstream of the point of desired application by any suitable means, such as by the use of a proportionating pump.
- the polymerization inhibitor can be added as a concentrate but it is preferable to add it as a solution which is compatible with the monomer being treated.
- Suitable solvents include kerosene, naphtha, the lower alkanes such as hexane, aromatic solvents, such as toluene, alcohols, polyols or ketones, etc.
- the concentration of polymerization inhibitor in the solvent is desirably in the range of about 1 to about 30 weight percent and preferably about 5 to about weight percent based on the total weight of inhibitor and solvent.
- the polymerization inhibitors herein are used at a concentration in the vinyl aromatic monomer which is effective to provide the desired protection against spontaneous polymerization. It has been determined that amounts of these derivatives in the range of from about 0.5 to about 1000 ppm based on the weight of the monomer being treated affords suitable protection against undesired polymerization. For most applications the inhibitor is used in amounts in the range of about 5 to about 500 ppm.
- the hydroxy derivatives of this invention can be employed as stabilizers for polymers that are susceptible to degradation, e.g., deterioration due to oxidation, elevated temperature and/or exposure to light or other actinic radiation.
- the hydroxyl derivatives can be introduced into the polymer employing any known and conventional method.
- polymers are poly-alpha-olefins such as polyethylene, polypropylene, polybutylene, and polyisoprene, copolymers of poly-alpha-olefins, polyamides, polyesters, polycarbonates, polyacetals, polystyrene, and conjugated diene polymers.
- polymers that can be stabilized by the hydroxyl derivatives of this invention include polyether polyols and polyurethane foams derived therefrom.
- the hydroxyl derivatives are added to the polymer in an amount sufficient to impart an appreciable stabilizing effect. In general, this amount may vary from about 0.1 to about 2 weight percent, preferably from about 0.2 to about 1 weight percent and more preferably from about 0.4 to about 0.6 weight percent by total weight of the polymer.
- This example illustrates the preparation of 1-hydroxy-2,2,4,6,6-pentamethyl-1,2,5,6-tetrahydropyrimidine (1-hydroxy acetonin).
- This example illustrates the preparation of 1-oxyl-2,2,4,6,6-pentamethyl-1,2,5,6-tetrahydropyrimidine (1-oxyl acetonin).
- This example illustrates the polymerization inhibitory effectiveness of the 1-hydroxy acetonin of Example 1 and the 1-oxyl acetonin of Example 2 in commercial grade styrene.
- the induction time was the amount of time required to make 1.00 weight percent polystyrene. (Time equals zero when the styrene solution reaches 118° C.) Thus, the longer the induction time, the greater the inhibiting ability of the material.
- This example illustrates the preparation of 1-oxyl-2,2,4,6,6-pentamethyl-1,2,5,6-tetrahydropyrimidine (acetonin nitroxyl).
- a reaction flask employed with a magnetic stirrer was charged with a solution of water containing 1.2 g (0.03 mole) sodium hydroxide, 4.6 g (0.03 mole) acetonin, 0.4 g Na 2 WO 4 and 0.4 g EDTA. 7 ml of hydrogen peroxide 30% was added in three portions at a temperature of 25° C. while efficiently stirring the clear solution. The temperature of the solution was increased to 35° C. giving an exothermic reaction with the temperature being further increased to 55° C. over a 10 to 20 minute period. The clear solution then turned to bright orange.
- This example illustrates the preparation of 1-hydroxy-2,2,4,6,6-pentamethyl-1,2,5,6-tetrahydropyrimidine (1-hydroxy acetonin).
- This example illustrates the preparation of 1-oxyl-2,2,4,6,6-pentamethyl-1,2,5,6-tetrahydropyrimidine (acetonin nitroxyl).
- This example illustrates the preparation of 1-hydroxy-2,2,4,6,6-pentamethyl-1,2,5,6-tetrahydropyrimidine (1-hydroxy acetonin).
- Ammonia from a balloon was bubbled into 60 ml (1.0 mole) acetone containing 0.4 g (0.004 mole) NaBr and 0.3 g (0.004 mole) NH 4 SCN for 5 hours. During the first hour, the reaction mixture was cooled in an ice bath and then the temperature was increased to ambient. The mixture was stirred for two hours and mixed with 30 ml of 50% aqueous NaOH.
- This example illustrates the preparation of 1-oxyl-2,2,4,6,6-pentamethyl-1,2,5,6-tetrahydropyrimidine (acetonin nitroxyl).
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
______________________________________ Concentration Induction Time Inhibitor (ppm) (minutes) ______________________________________ 1-hydroxy acetonin 100 28 1-oxyl acetonin 100 43 no inhibitor -- 5 ______________________________________
Claims (30)
Priority Applications (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/816,630 US5847035A (en) | 1997-03-13 | 1997-03-13 | Substituteed tetrahydropyrimidine derivatives and their use as polymerization inhibitors for vinyl aromatic compounds |
AU66760/98A AU6676098A (en) | 1997-03-13 | 1998-03-02 | Substituted tetrahydropyrimidine derivatives and their use as polymerization inhibitors for vinyl aromatic compounds |
AT98908819T ATE259790T1 (en) | 1997-03-13 | 1998-03-02 | SUBSTITUTED TETRAHYDROPYRIMIDINE DERATIVES AND THEIR USE AS POLYMERIZATION INHIBITORS FOR VINYL AROMATIC COMPOUNDS |
EP98908819A EP0968192B1 (en) | 1997-03-13 | 1998-03-02 | Substituted tetrahydropyrimidine derivatives and their use as polymerization inhibitors for vinyl aromatic compounds |
CA002283585A CA2283585C (en) | 1997-03-13 | 1998-03-02 | Substituted tetrahydropyrimidine derivatives and their use as polymerization inhibitors for vinyl aromatic compounds |
DE69821744T DE69821744T2 (en) | 1997-03-13 | 1998-03-02 | SUBSTITUTED TETRAHYDROPYRIMIDINE DERATIVE AND THEIR USE AS A POLYMERIZATION INHIBITOR FOR VINYL AROMATIC COMPOUNDS |
ES98908819T ES2216275T3 (en) | 1997-03-13 | 1998-03-02 | DERIVATIVES OF SUBSTITUTED TETRAHYDROPIRIMIDINE AND ITS USE AS POLYMERIZATION INHIBITORS FOR VINYL AROMATIC COMPOUNDS. |
PT98908819T PT968192E (en) | 1997-03-13 | 1998-03-02 | SUBSTITUTED TETRA-HYDROPYRIMIDINE DERIVATIVES AND THEIR USE AS POLYMERIZATION INHIBITORS FOR VINYL AROMATIC COMPOUNDS |
PCT/US1998/003983 WO1998040360A1 (en) | 1997-03-13 | 1998-03-02 | Substituted tetrahydropyrimidine derivatives and their use as polymerization inhibitors for vinyl aromatic compounds |
KR1019997007485A KR20000071195A (en) | 1997-03-13 | 1998-03-02 | Substituted tetrahydropyrimidine derivatives and their use as polymerization inhibitors for vinyl aromatic compounds |
JP53960998A JP3282830B2 (en) | 1997-03-13 | 1998-03-02 | Substituted tetrahydropyrimidine derivatives and their use as polymerization inhibitors for vinyl aromatic compounds |
TW087103762A TW512148B (en) | 1997-03-13 | 1998-03-17 | Substituted tetrahydropyrimidine compounds, compositions containing same and methods using the compounds |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/816,630 US5847035A (en) | 1997-03-13 | 1997-03-13 | Substituteed tetrahydropyrimidine derivatives and their use as polymerization inhibitors for vinyl aromatic compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
US5847035A true US5847035A (en) | 1998-12-08 |
Family
ID=25221199
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US08/816,630 Expired - Lifetime US5847035A (en) | 1997-03-13 | 1997-03-13 | Substituteed tetrahydropyrimidine derivatives and their use as polymerization inhibitors for vinyl aromatic compounds |
Country Status (12)
Country | Link |
---|---|
US (1) | US5847035A (en) |
EP (1) | EP0968192B1 (en) |
JP (1) | JP3282830B2 (en) |
KR (1) | KR20000071195A (en) |
AT (1) | ATE259790T1 (en) |
AU (1) | AU6676098A (en) |
CA (1) | CA2283585C (en) |
DE (1) | DE69821744T2 (en) |
ES (1) | ES2216275T3 (en) |
PT (1) | PT968192E (en) |
TW (1) | TW512148B (en) |
WO (1) | WO1998040360A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006110112A3 (en) * | 2005-04-15 | 2007-03-22 | Sun Ace Kakoh Pte Ltd | Stabiliser composition for halide-containing polymers |
US20090030123A1 (en) * | 2005-04-15 | 2009-01-29 | Sun Ace Kakoh (Pte.) Ltd. | Stabiliser composition for halide-containing polymers |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR112013015539A2 (en) | 2010-12-20 | 2016-09-20 | Dow Global Technologies Llc | composition and method for bonding two or more substrates together |
WO2013077908A1 (en) * | 2011-11-23 | 2013-05-30 | Dow Global Technologies Llc | Curable compositions containing isocyanate functional components and having improved durability in the cured state |
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-
1997
- 1997-03-13 US US08/816,630 patent/US5847035A/en not_active Expired - Lifetime
-
1998
- 1998-03-02 WO PCT/US1998/003983 patent/WO1998040360A1/en not_active Application Discontinuation
- 1998-03-02 KR KR1019997007485A patent/KR20000071195A/en not_active Application Discontinuation
- 1998-03-02 DE DE69821744T patent/DE69821744T2/en not_active Expired - Lifetime
- 1998-03-02 CA CA002283585A patent/CA2283585C/en not_active Expired - Fee Related
- 1998-03-02 ES ES98908819T patent/ES2216275T3/en not_active Expired - Lifetime
- 1998-03-02 AU AU66760/98A patent/AU6676098A/en not_active Abandoned
- 1998-03-02 PT PT98908819T patent/PT968192E/en unknown
- 1998-03-02 AT AT98908819T patent/ATE259790T1/en not_active IP Right Cessation
- 1998-03-02 EP EP98908819A patent/EP0968192B1/en not_active Expired - Lifetime
- 1998-03-02 JP JP53960998A patent/JP3282830B2/en not_active Expired - Fee Related
- 1998-03-17 TW TW087103762A patent/TW512148B/en not_active IP Right Cessation
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006110112A3 (en) * | 2005-04-15 | 2007-03-22 | Sun Ace Kakoh Pte Ltd | Stabiliser composition for halide-containing polymers |
US20090030123A1 (en) * | 2005-04-15 | 2009-01-29 | Sun Ace Kakoh (Pte.) Ltd. | Stabiliser composition for halide-containing polymers |
US7842743B2 (en) | 2005-04-15 | 2010-11-30 | Sun Ace Kakoh (Pte.) Ltd. | Stabiliser composition for halide-containing polymers |
EA015567B1 (en) * | 2005-04-15 | 2011-10-31 | Сун Асе Какох (Пте.) Лтд. | Stabilizer composition for halide-containing polymers (variants), polymer compositions, a method for obtaining and stabilising polymers |
Also Published As
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AU6676098A (en) | 1998-09-29 |
EP0968192A1 (en) | 2000-01-05 |
KR20000071195A (en) | 2000-11-25 |
ATE259790T1 (en) | 2004-03-15 |
TW512148B (en) | 2002-12-01 |
EP0968192B1 (en) | 2004-02-18 |
JP2000511563A (en) | 2000-09-05 |
CA2283585A1 (en) | 1998-09-17 |
JP3282830B2 (en) | 2002-05-20 |
CA2283585C (en) | 2009-01-20 |
WO1998040360A1 (en) | 1998-09-17 |
DE69821744T2 (en) | 2004-12-09 |
DE69821744D1 (en) | 2004-03-25 |
PT968192E (en) | 2004-05-31 |
ES2216275T3 (en) | 2004-10-16 |
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